In the landscape business, as in life, nothing is as simple as it seems.

You work your tail off getting your business started in the hopes that it will earn you a comfortable living. Yet you find that with growth comes more staff, more equipment, and more headaches. You hope that your headaches will be offset by greater profitability. Then, as you settle in for the long haul, it’s still a constant challenge to run your business efficiently.

Very few landscape contractors who started their business 20 and 30 years ago had any formal training in the business end of the business. They had to learn the hard way—by doing. In recent years, consultants who know our industry have become available to help.

There are times when you’re buffeted by conditions beyond your control. (Ask anyone who was expecting to do snow removal last winter but saw their plow-equipped trucks sit idle). For better or for worse, customer economics become your economics.

In the best of all possible worlds, you’ll reach the point where you’ve got a successful business and you’re ready to slow down a bit. You might even be ready to pass the operational baton to the next generation. That next generation often turns out to be our sons and daughters who’ve worked with us and want to run the company when we’re ready to hand over the reins.

Alas, this is not as simple as it seems. It’s certainly not a matter of tossing the keys to the kids and walking out the door. There are major issues to consider: financial, operational, and emotional.

There are a number of firms that can help contractors with structuring the business side. One company, LandOpt in Pittsburgh, Pennsylvania, can help in the transition. They are a service organization that helps landscape contractors implement proven business systems.

Following are the experiences of two landscape firms now making a generational transition...